Entrepreneur on the Island: A Conversation with Paul Jarvis


Cameron McCool


Reviewed by


June 3, 2016

This article is Tax Professional approved


Despite living deep in the woods on a remote island, Paul Jarvis is relentlessly productive.

During his 17-year career as a freelance entrepreneur, Paul has launched a diverse portfolio of products and businesses that spans online courses, software products, a respected body of writing, and two podcasts.

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At the time of our interview, Paul was managing Creative Class, a course that helps freelancers better run their business, while simultaneously developing ofCourseBooks, a software platform for course makers. Days before we published this feature, he launched Emojibombs, a platform that emails daily emoji stories to your inbox, which he built in a single day using MailChimp, Stripe, and Wordpress.

A common aspect found in all of Paul’s creations is the motivation to delight and support others in their pursuit of success. In a sense, he is the Pied Piper of many modern entrepreneurs.

Curious to learn how prolonged remote-based entrepreneurship has affected his personal lifestyle and his experience in business, we spent a day with Paul at his home on Vancouver Island.


Why did you choose an island as your remote base?

My wife and I had just had enough of the city. We did our time in the rat race, and we wanted something different. Luckily, I can work from anywhere. Even when I lived in big cities, I rarely met the clients that I work with or the people that I work with, so it’s no different now.

The support of your significant other forms such an integral part of success in entrepreneurship. What does your wife make of your remote-based business?

I don’t think she knows exactly what I do, but she likes it, because she also enjoys to be in the middle of nowhere. When we moved to Tofino, she was a surf instructor. When she wanted to go to school in South Island, I was like “It doesn’t matter to me, let’s do it.” Because I can go anywhere, it doesn’t matter to me where we’re based. I’m basically a trailing spouse.

I’m most productive when I listen to myself. Introspection is difficult, but it pays off.


What misconceptions do people hold about your remote-based lifestyle?

There’s this vision of the modern solo entrepreneur. They’re a nomad, they have a backpack with their 37 items in it, they go anywhere, and they are sipping a pina colada with one hand while they type an epic blog post with the other. I actually know some people who live fairly similar to that description, but most of the entrepreneurs I know don’t live like that at all. Those stories just sound sexier than, say, a story about me sitting in my house all day in my sweatpants.

Has living on an island influenced your approach to business?

Living remotely—literally and figuratively—there’s a greater need for DIY. I have friends that live in LA who they can basically hire somebody on TaskRabbit to come to their house and fix something, or run errands. When you’re remote, there’s nobody to do things for you, so you have to do a lot for yourself. I really like that. The do-it-yourself attitude is how I live my life, and I approach business in the same way. So it all kind of flows together.

What does a typical day look like for you?

There is no typical structure to my day. I wake up and I figure out what’s reasonable for me to accomplish during the day. And if there is something specific I’m working on, like launching a software product, then I know, “Okay, I need to get this done by this date or the developer or the operations guy can’t do their job.” I focus on that.

I typically have to do a bunch of writing everyday, but that happens kind of whenever, usually after I record content for my podcasts, Invisible Office Hours and the freelancer. I also break my day up. If I’m sore from talking, then I switch to writing, or I’ll go outside and work in the garden.

I know what I need to get done, and then I do it whenever I need to, to accomplish it in on that day. My approach is scary for some people. But it’s scary to me to see some friends regiment their schedule down to 15-minute increments. I watch that and think: I would suffocate.


Regiment and structure are often touted as a surefire methods for maintaining productivity. Why does not having a set routine work well for you?

The reason that I still work for myself after 17 years is because I can have a business that I actually like to have. I can structure it in a way that works just for me and it probably wouldn’t work for anybody else.

When people first start working for themselves, they often think that they need to model their routine after the way business has been done in the past, or in a way that a thought leader on the Internet says they should in order to make like six figures in a single day.

In reality, a lot of the times we’re most productive is when we listen to ourselves with our own cues, rather than following prescriptions from other well-intentioned people.

You probably don’t adhere to a typical nine-to-five schedule, then?

No. I follow my body’s rhythm. I can get the most out of the day when I respect it, and when I give it what it needs, whether that’s exercise or working on specific times of the day. I pay attention to that, but my days are never guided by a set schedule.


The ability to shape your schedule based on your body’s needs is one of the nicer perks of remote entrepreneurship.

True. For me, if it’s nice out and I can get outside then I’ll work from 6am to 10am, and then again from 6:00pm to 10:00pm because I would rather spend my day outside if it’s nice out, and then get the work done in between or work a bit in the weekends.

But scheduling like that isn’t common practice. A lot of people who work for themselves because they’re fed up with the nine-to-five end up working nine-to-five hours anyways. They just get into a mindset of, “I don’t want to do this type of life anymore, but I’m still going to adhere to the rules of that type of life anyways.”

When you work remotely, you don’t have to do that.


Do entrepreneurs need certain attributes to succeed in remote-based business?

You definitely need to figure out what motivates you. You have to have that locked in. And you have to be motivated on demand. It’s like being creative on demand. You need to be able to work if the situation calls for it.

I’ve been a designer for 20 years. If I don’t feel like designing and I have a deadline, I’ve just got to turn it on and do it, otherwise I’m going to miss deadlines, my clients are going to hate me, and I’m not going to have a great reputation.

When you’re remote-based, there’s nobody looking over your shoulder. There’s nobody typically checking in. So you need to make sure that you’re working to or ahead of your schedule at all times.

There are certain challenges that are unique to working remotely. One of Bench’s designers is telecommuting from New York this month. Unreliable wifi has been the bane of her existence since she arrived. What remote-work challenges have you had to overcome?

I can relate to that. The internet connection in Tofino was so bad. Even if you work remotely from major cities, you’ll never escape remote-work problems. Once when I was working in Vancouver, the power went out for three days. When you’re remote-based, you need to accept that there will always be situations that are completely out of your control. First, you have to own it, and second, you have to deal with it.

I always say “Life is going to shit on your face, and you never know when. You just have to make sure your mouth is closed.” Things happen and things come up. You just have to solve them.


Even though you live deep in the woods on a remote island, you’ve forged some close friendships and professional relationships with big names in your niche. How do you build relationships from afar?

It’s more organic than people think. I connect with influencers the same way I connect with new friends. For example, all of the people that I know that have big audiences, they’re still all human beings. All of them just want to have a good, engaging conversation. And I think a lot of the influencers that I’ve befriended, we started out by connecting on the most random things.

The biggest podcast that I was ever on (Srinivas Rao, The Unmistakable Creative), I was on it because the host is a surfer. I’m a surfer, and surfers love talking about surfing. So we connected over that. When you share similarities with somebody that has dealt with the same things as you, a relationship can grow easily from there. You do have to make an effort, but not in a way where you aim to make fake, vapid, ephemeral connections with people.

As a remote entrepreneur, you have to put extra effort into connecting with others, because you’re not going to bump into somebody when you’re working from afar. That never happens out here.

You also have to maintain relationships and stay in touch with people. I have time scheduled in my calendar on the first or the second day of every month to connect with people. It says in my calendar, “Ping people.” And when I get that notification, I try to think “Who haven’t I talked to in a while that I miss? Who do I actually want to talk to?” Then I email those people.

As a remote entrepreneur, you have to put extra effort into connecting with others, because you’re not going to bump into somebody when you’re working from afar.


Does being remote-based exacerbate a fear of missing out?

No. I guess it could. Generally, I just wish I was outside more. When the weather is nice, I look out the window and think “Oh, I’m missing out on this awesome weather.” I don’t think I’ve ever thought “Oh, I missed this conference,” or, “I missed this thing happening.”

Have you ever taken a huge risk to move your business forward?

I have. Quite a few times. Most recently it was—like I had a very successful career as a designer. I had dialed in with the niche that I worked in and then I was like, “What if I make products and do that instead?” I thought, “I don’t know if this is going to work but let’s see.”

More recently was the decision to launch Invisible Office Hours, the podcast that I host with Jason Zook. We had three seasons where it was just him and I talking on a topic and that went really well. We had sponsors lined up. We had a good audience. People were stoked about it. And then we said, “For season four let’s build a software product and every episode is going to be about this software product.” So, I don’t know. I guess that’s my form of adrenaline. Taking creative risks is fun.


Is there a particular piece of advice that’s served you well in business?

Yeah. I think probably the biggest one is that like if your boss is an asshole and you work for yourself, something has got to change. This is something that I’ve struggled with and worked out for my whole career as well, that you can do business in a way that suits you that isn’t the same as what everybody else is doing.

Do you hire contractors to help with your output?

Oh, I definitely do. I hire them specifically because I don’t have to tell them what to do.

Take my copy editor, Matt. I just send him my articles and he knows exactly what needs to be done. It’s the reason I hired him and not somebody else. He didn’t have any questions. He just got the job done.

It’s the same with the sound engineer of my two podcasts, the freelancer and Invisible Office Hours. He doesn’t ask us things, because he’s the expert. My accountant and my lawyer are the same. They just say “This is your bill, this is what we did.” And that’s it.

It sounds like when you find the perfect hairdresser: you sit down in the chair, they cut your hair, and the final result is great every single time.

Yes. Except I cut my own hair. There are no hairdressers here.

Complete DIY.


Everything in my house is so beautiful. And then I have my Herman Miller chair and desk in a rat pen.


Can we talk about your pet rats?

Sure. I have two right now, Luna and Osha. I built a pen for them around my desk. So, technically, my home office is inside their room.

Why did you build your rats’ pen around your workspace?

I wanted them to be free. They have a cage, which they love, but I wanted them to be able to run around. Their pen is made out of corrugated plastic. It’s version five or six of this pen, because they keep outsmarting me. If they can find a way out of something they will.

So you just keep modifying the enclosure until they hack their way out of it again?

Exactly. It’s iterative. The rat pen is iterative.

Crew Founder Mikael Cho told us that owning a dog helped him to achieve a better work-life balance, because it made him get outdoors more often. Has rat ownership had an influence on your work-life balance?

They do help me to take a lot of breaks. They’re very interactive animals, and they need attention. In the morning when I get up, I can’t just hop online and start working. I have to have play with them, and one of them needs to cuddle for a while. I also take time off to prepare their meals. They eat vegan, raw, organic food that I make from scratch.

A lot of times, the life we think we want and the life we actually want are very different.


What advice would you offer entrepreneurs who are interested in launching a remote-based business?

You need to iterate on the life that you want. A lot of times, the life we think we want and the life we actually want are very different. It’s okay to dabble with how you want to live, and it’s okay to figure it out as you go. I moved probably 12 or 13 times in the last, I don’t know, 10, 11 years? We’ve moved so many times because we were figuring stuff out.

To do that successfully until you find a remote-based setup that works for you, you need to avoid beating yourself up if something isn’t working. And you need to avoid resting on your laurels if something is working, because things are going to change again soon enough.

Paul Jarvis is the founder of Creative Class, a course to help freelancers better run their business, and ofCourseBooks, software for online course makers. Paul also presents the podcasts Invisible Office Hours and the freelancer.

Subscribe to his weekly newsletter, The Sunday Dispatches, and connect with Paul on Twitter.

This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.
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